Catalytic Asymmetric Synthesis of Diketopiperazines by Intramolecular Tsuji–Trost Allylation | Zendy

Matteo Faltracco | Zendy; Silvia Cotogno | Zendy; Christophe M. L. Vande Velde | Zendy; Eelco Ruijter | Zendy

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Catalytic Asymmetric Synthesis of Diketopiperazines by Intramolecular Tsuji–Trost Allylation

Author(s) -

Matteo Faltracco,

Silvia Cotogno,

Christophe M. L. Vande Velde,

Eelco Ruijter

Publication year - 2019

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.9b01994

Subject(s) - diketopiperazines , chemistry , intramolecular force , yield (engineering) , catalysis , adduct , enantioselective synthesis , combinatorial chemistry , organic chemistry , materials science , metallurgy

We report the intramolecular Tsuji-Trost reaction of Ugi adducts to give spiro-diketopiperazines in high yield and with high enantioselectivity. This approach allows the catalytic asymmetric construction of a broad range of these medicinally important heterocycles under mild conditions, in two steps from cheap, commercially available starting materials.

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